WILLY [with pity and resolve]: I’ll see him in the morning; I’ll have a nice talk with him. I’ll get him a job selling. He could be big in no time. My God! Remember how they used to follow him around in high school? When he smiled at one of them their faces lit up. When he walked down the street… [He loses himself in reminiscences.] (Act 1)
Willy attributes Biff's former popularity and success to his smile. Now, however, it seems that Biff's smile and good looks just haven't been enough to get him to a stable place in life. Yes, it seems that Biff's attractiveness just hasn't gotten him that far.
WILLY: I’m fat. I’m very—foolish to look at, Linda. I didn’t tell you, but Christmas time I happened to be calling on F.H. Stewarts, and a salesman I know, as I was going in to see the buyer I hear him say something about—walrus. And I—I cracked him right across the face. I won’t take that. I simply will not take that. But they do laugh at me. I know that.
WILLY: I gotta overcome it. I know I gotta overcome it. I’m not dressing to advantage, maybe. (Act 1)
Willy assumes his business problems have to do primarily with his appearance. It doesn't seem to occur to him that his real problem may be that people see right through his flimsy, image-obsessed personality. The play may be pointing out that people of real substance are the ones who get real respect.
BIFF [deciding]: Lend me ten bucks, will ya? I want to buy some new ties.
HAPPY: I’ll take you to a place I know. Beautiful stuff. Wear one of my stripped shirts tomorrow. (Act 1)
Biff and Happy's emphasis on Biff's appearance distracts them from more relevant reality (the fact that Oliver won't recognize Biff). They've somehow deluded themselves into believing that, if Biff looks good enough, Oliver will start forking over the money—even though he hasn't seen Biff in years.
HAPPY [enthralled]: That’s what I dream about Biff. Sometimes I wanna just rip my clothes off in the middle of the store and outbox that goddamned merchandise manager. I mean I can outbox, outlift and outrun anybody in that store, and I have to take orders from those petty, common sons of b****es till I can’t stand it anymore. (Act 1)
Happy's compulsion to tear off his clothes and attack his coworkers in the office may reflect his frustration with the importance of appearances. Though Happy is pretty obsessed with looking good himself, it seems that sometimes he wants to rip it all away and act like an animal.
WILLY: He’s heading for a change. There’s no question, there simply are certain men that take longer to get—solidified. How did he dress?
LINDA: His blue suit. He’s so handsome in that suit. He could be a—anything in that suit! (Act 2)
Once again we see that Linda and Willy's fixation on Biff's physical appearance as the source of his success denies the importance of other qualities and virtues. They seem to have completely forgotten that Biff once stole from Oliver and that that might matter more than the fact that he's now wearing a nice suit.
WILLY: Yeah. Sing to me. [Linda hums a soft lullaby]. When that team came out—he was the tallest, remember?
LINDA: Oh, yes. And in gold. (Act 2)
Willy and Linda place great importance on Biff's appearance when he was a high school football star, as if that had something to do with his talent. The very fact that he was so attractive made them positive that he would one day be successful.